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Cheap flights from Santa Rosa to Chicago from $144

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Santa Rosa to Chicago departing on 11/8. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Santa Rosa to Chicago

Cheap round-trip flights

Alaska Airlines Logo
8:00 am - 6:54 pmSTS-ORD
8h 54m1 stop
Alaska Airlines Logo
3:05 pm - 11:08 pmORD-STS
10h 03m1 stop
$277Alaska Airlines
Find Deal
Fri, Dec 5 - Mon, Dec 8
Alaska Airlines Logo
9:43 am - 11:59 pmSTS-ORD
12h 16m2 stops
Alaska Airlines Logo
9:20 am - 4:02 pmORD-STS
8h 42m1 stop
$283Alaska Airlines
Find Deal
Tue, Oct 21 - Tue, Oct 28
Alaska Airlines Logo
9:43 am - 11:59 pmSTS-ORD
12h 16m2 stops
Alaska Airlines Logo
9:20 am - 9:46 pmORD-STS
14h 26m2 stops
$289Alaska Airlines
Find Deal
Tue, Oct 21 - Wed, Oct 29
Alaska Airlines Logo
9:43 am - 11:59 pmSTS-ORD
12h 16m2 stops
Alaska Airlines Logo
3:50 pm - 11:16 pmORD-STS
9h 26m1 stop
$293Alaska Airlines
Find Deal
Tue, Oct 7 - Tue, Oct 14
Alaska Airlines Logo
7:46 pm - 1:54 pmSTS-ORD
16h 08m1 stop
Alaska Airlines Logo
9:20 am - 4:02 pmORD-STS
8h 42m1 stop
$297Alaska Airlines
Find Deal
Mon, Nov 10 - Wed, Nov 12
Alaska Airlines Logo
7:46 pm - 1:54 pmSTS-ORD
16h 08m1 stop
Alaska Airlines Logo
9:20 am - 9:46 pmORD-STS
14h 26m2 stops
$304Alaska Airlines
Find Deal
Mon, Nov 10 - Wed, Nov 12
Alaska Airlines Logo
7:53 pm - 6:59 pmSTS-ORD
21h 06m1 stop
Alaska Airlines Logo
3:50 pm - 11:16 pmORD-STS
9h 26m1 stop
$308Alaska Airlines
Find Deal
Tue, Oct 7 - Tue, Oct 14
Alaska Airlines Logo
7:50 am - 11:59 pmSTS-ORD
14h 09m2 stops
Alaska Airlines Logo
3:05 pm - 11:08 pmORD-STS
10h 03m1 stop
$311Alaska Airlines
Find Deal
Sat, Dec 6 - Thu, Dec 11
Alaska Airlines Logo
6:43 pm - 6:54 pmSTS-ORD
22h 11m1 stop
Alaska Airlines Logo
3:05 pm - 11:08 pmORD-STS
10h 03m1 stop
$317Alaska Airlines
Find Deal
Tue, Dec 2 - Fri, Dec 5
Alaska Airlines Logo
7:46 pm - 1:54 pmSTS-ORD
16h 08m1 stop
Alaska Airlines Logo
2:54 pm - 11:57 pmORD-STS
11h 03m1 stop
$318Alaska Airlines
Find Deal
Mon, Nov 17 - Wed, Nov 19

Alaska Airlines flights from Santa Rosa to Chicago

Our best Alaska Airlines deals on Santa Rosa to Chicago flight tickets
Alaska Airlines
Dec 5
STS8:00 amSanta Rosa Sonoma County
8h 54m
1 stop
ORD6:54 pmChicago O'Hare Intl
Dec 8
ORD3:05 pmChicago O'Hare Intl
10h 03m
1 stop
STS11:08 pmSanta Rosa Sonoma County
$277
Find similar
Alaska Airlines
Oct 21
STS9:43 amSanta Rosa Sonoma County
12h 16m
2 stops
ORD11:59 pmChicago O'Hare Intl
Oct 28
ORD9:20 amChicago O'Hare Intl
8h 42m
1 stop
STS4:02 pmSanta Rosa Sonoma County
$283
Find similar
Alaska Airlines
Oct 21
STS9:43 amSanta Rosa Sonoma County
12h 16m
2 stops
ORD11:59 pmChicago O'Hare Intl
Oct 29
ORD9:20 amChicago O'Hare Intl
14h 26m
2 stops
STS9:46 pmSanta Rosa Sonoma County
$289
Find similar

Hawaiian Airlines flights from Santa Rosa to Chicago

Our best Hawaiian Airlines deals on Santa Rosa to Chicago flight tickets
Hawaiian Airlines
Sep 22
STS2:28 pmSanta Rosa Sonoma County
7h 35m
1 stop
ORD12:03 amChicago O'Hare Intl
Sep 28
ORD8:00 amChicago O'Hare Intl
7h 36m
1 stop
STS1:36 pmSanta Rosa Sonoma County
$821
Find similar
Hawaiian Airlines
Sep 18
STS7:00 amSanta Rosa Sonoma County
7h 49m
1 stop
ORD4:49 pmChicago O'Hare Intl
Sep 20
ORD6:20 amChicago O'Hare Intl
9h 16m
1 stop
STS1:36 pmSanta Rosa Sonoma County
$958
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Santa Rosa to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated September 16, 2025.
Use the filters below to find and compare flights from Santa Rosa to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Fri 12/5

8:00 am-6:54 pm

1 stop8h 54m

Chicago O'Hare Intl

Mon 12/8

3:05 pm-11:08 pm

1 stop10h 03m

$277

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Tue 10/21

9:43 am-11:59 pm

2 stops12h 16m

Chicago O'Hare Intl

Tue 10/28

9:20 am-4:02 pm

1 stop8h 42m

$283

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Tue 10/21

9:43 am-11:59 pm

2 stops12h 16m

Chicago O'Hare Intl

Wed 10/29

9:20 am-9:46 pm

2 stops14h 26m

$289

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Tue 10/7

9:43 am-11:59 pm

2 stops12h 16m

Chicago O'Hare Intl

Tue 10/14

3:50 pm-11:16 pm

1 stop9h 26m

$293

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Mon 11/10

7:46 pm-1:54 pm

1 stop16h 08m

Chicago O'Hare Intl

Wed 11/12

9:20 am-4:02 pm

1 stop8h 42m

$297

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Mon 11/10

7:46 pm-1:54 pm

1 stop16h 08m

Chicago O'Hare Intl

Wed 11/12

9:20 am-9:46 pm

2 stops14h 26m

$304

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Tue 10/7

7:53 pm-6:59 pm

1 stop21h 06m

Chicago O'Hare Intl

Tue 10/14

3:50 pm-11:16 pm

1 stop9h 26m

$308

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Sat 12/6

7:50 am-11:59 pm

2 stops14h 09m

Chicago O'Hare Intl

Thu 12/11

3:05 pm-11:08 pm

1 stop10h 03m

$311

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Tue 12/2

6:43 pm-6:54 pm

1 stop22h 11m

Chicago O'Hare Intl

Fri 12/5

3:05 pm-11:08 pm

1 stop10h 03m

$317

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Mon 11/17

7:46 pm-1:54 pm

1 stop16h 08m

Chicago O'Hare Intl

Wed 11/19

2:54 pm-11:57 pm

1 stop11h 03m

$318

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Santa Rosa to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $403. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Santa Rosa to Chicago for around $514.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Santa Rosa to Chicago during this time can be as low as $413. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $466.

When to book flights from Santa Rosa to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Santa Rosa to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Santa Rosa to Chicago (STS to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Santa Rosa to Chicago

Direct flights

None
There are no direct flights from Santa Rosa to Chicago. There are no popular flight routes from Santa Rosa to Chicago.
Search flight deals

  • How far is Santa Rosa Sonoma County to Chicago by plane?

    There are 1853.6 mi between Santa Rosa Sonoma County and Chicago. In terms of flight time, this usually takes a little over 6h 58m.

  • When did momondo last update prices for flights from Santa Rosa Sonoma County Airport to Chicago?

    Prices for flights from Santa Rosa Sonoma County Airport to Chicago refresh daily.

  • How many operators does momondo search for flights from Santa Rosa Sonoma County Airport to Chicago?

  • How old do you have to be to fly from Santa Rosa Sonoma County Airport to Chicago?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Santa Rosa Sonoma County Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular airline from Santa Rosa to Chicago?

Best airlines flying from Santa Rosa to Chicago

Compare and see reviews for airlines that fly from Santa Rosa to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Alaska AirlinesPriceFrom $308Free CancellationRating
8.0
10,000 reviews
Search Alaska Airlines flights
American AirlinesPriceFrom $316Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Santa Rosa to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Santa Rosa to Chicago. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Santa Rosa to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Santa Rosa with this policy.

How can momondo help me find flights from Santa Rosa to Chicago?

momondo helps you find the best flight between Santa Rosa and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Santa Rosa to Chicago right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Santa Rosa to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport